Piperidine → HCID 7190323, compound

HRID 715731Notes

Reaction equation

HRID 715731 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:10]2[N:11]=[C:12]([S:15][CH2:16][C:17]([OH:19])=O)[CH:13]=[CH:14][C:9]2=[N:8][N:7]=1.CN(C(ON1N=N[C:30]2[CH:31]=[CH:32][CH:33]=[N:34][C:29]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.N1CCCCC1.CCN(C(C)C)C(C)C>CN(C=O)C>[N:34]1([C:17](=[O:19])[CH2:16][S:15][C:12]2[CH:13]=[CH:14][C:9]3[N:10]([C:6]([C:2]4[S:1][CH:5]=[CH:4][CH:3]=4)=[N:7][N:8]=3)[N:11]=2)[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]1

Participants

6

Reactant 4

HCID 8082PiperidineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 43935798HCID 43935798, compound

Product 1

HCID 7190323HCID 7190323, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 2-((3-(thiophen-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)thio)acetic acid (100 mg, 0.34 mmol) dissolved in DMF (3 mL) was added HATU (150 mg), and after 15 minutes stirring, piperidine (40 mg) was added followed by DIPEA (200 μL). The mixture was stirred for room temperature overnight and then evaporated to dryness. 1-(Piperidin-1-yl)-2-((3-(thiophen-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)thio)ethanone was then isolated by preparative TLC (silica gel plates, 9:1 CHCl3/MeOH).

Workup

  1. stirringThe mixture was stirred for room temperature overnight
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-482ca856b12147898e51323471dcf672
Source dataset
uspto-grants-2015_11
Patent number
US09187484B2

Reaction notes

Loading…